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Ethenyl indoles as neutral hydrophobic fluorescence probes
Author(s) -
Singh Anil K.,
Hota Prasanta K.
Publication year - 2007
Publication title -
journal of physical organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.325
H-Index - 66
eISSN - 1099-1395
pISSN - 0894-3230
DOI - 10.1002/poc.1222
Subject(s) - chemistry , fluorescence , quantum yield , substituent , bovine serum albumin , indole test , photochemistry , fluorescence in the life sciences , solvent , ligand (biochemistry) , quenching (fluorescence) , fluorescence spectroscopy , stereochemistry , organic chemistry , chromatography , biochemistry , physics , receptor , quantum mechanics
3‐(4‐Nitrophenylethenyl‐ E )‐NH‐indole ( 1 ), 3‐(4‐nitrophenyl ethenyl‐ E )‐ N ‐acetylindole ( 2 ), and 3‐(4‐nitrophenylethenyl‐ E )‐ N ‐benzenesulfonylindole ( 3 ) are relatively less fluorescent in organic solvents, with fluorescence quantum yield (Φ f ) in the range of 0.002 to 0.066 depending on the solvent polarity. However, in bovine serum albumin (BSA)‐phosphate buffer, the fluorescence of these compounds gets drastically enhanced with Φ f in the range of 0.21 to 0.67, depending on the substituent on the indolic nitrogen atom. Additionally, linear increase in the fluorescence intensity of 2 and 3 occurs on increasing the BSA concentration. These fluorescence properties together with the neutral, hydrophobic nature of these compounds make these fluorophores good fluorescence probe for studying the micropolarity of proteins like BSA and in general the ligand–protein interactions. Copyright © 2007 John Wiley & Sons, Ltd.